2-methoxyethanol (CHEBI:46790)

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CHEBI:46790 - 2-methoxyethanol

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ChEBI Name	2-methoxyethanol

ChEBI ID	CHEBI:46790

Definition	A hydroxyether that is ethanol substituted by a methoxy group at position 2.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:19677, CHEBI:44217

Supplier Information	ChemicalBook:CB9319046, eMolecules:883948

Download	Molfile XML SDF

more structures >>

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13 12 0 0 0 0 999 V2000

1.7810 -0.7194 0.0912 O 0 0 0 0 0 0 0 0 0 0 0 0

0.7431 -0.8744 -0.8780 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.5958 -0.4673 -0.2621 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.5333 0.8975 0.1550 O 0 0 0 0 0 0 0 0 0 0 0 0

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2.6055 -0.9862 -0.3365 H 0 0 0 0 0 0 0 0 0 0 0 0

0.6953 -1.9159 -1.1964 H 0 0 0 0 0 0 0 0 0 0 0 0

0.9542 -0.2411 -1.7397 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.8069 -1.1006 0.5996 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.3868 -0.5854 -1.0015 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.8071 2.2531 1.0530 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.5825 1.0772 -0.0330 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.0018 0.5615 1.5679 H 0 0 0 0 0 0 0 0 0 0 0 0

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1 6 1 0 0 0 0

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3 4 1 0 0 0 0

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Wikipedia	License
2-Methoxyethanol, or methyl cellosolve, is an organic compound with formula C3H8O2 that is used mainly as a solvent. It is a clear, colorless liquid with an ether-like odor. It is in a class of solvents known as glycol ethers which are notable for their ability to dissolve a variety of different types of chemical compounds and for their miscibility with water and other solvents. It can be formed by the nucleophilic attack of methanol on protonated ethylene oxide followed by proton transfer: C2H5O+ + CH3OH → C3H8O2 + H+ 2-Methoxyethanol is used as a solvent for many different purposes such as varnishes, dyes, and resins. It is also used as an additive in airplane deicing solutions. In organometallic chemistry it is commonly used for the synthesis of Vaska's complex and related compounds such as carbonylchlorohydridotris(triphenylphosphine)ruthenium (II). During these reactions the alcohol acts as a source of hydride and carbon monoxide. 2-Methoxyethanol is toxic to the bone marrow and testicles. Workers exposed to high levels are at risk for granulocytopenia, macrocytic anemia, oligospermia, and azoospermia. The methoxyethanol is converted by alcohol dehydrogenase into methoxyacetic acid which is the substance which causes the harmful effects. Both ethanol and acetate have a protecting effect. The methoxyacetate can enter the Krebs cycle where it forms methoxycitrate.
Read full article at Wikipedia

Formula

C3H8O2

Net Charge

Average Mass

76.09442

Monoisotopic Mass

76.05243

InChI

InChI=1S/C3H8O2/c1-5-3-2-4/h4H,2-3H2,1H3

InChIKey

XNWFRZJHXBZDAG-UHFFFAOYSA-N

SMILES

COCCO

Roles Classification
Chemical Role(s):	protic solvent A polar solvent that is capable of acting as a hydron (proton) donor. (via glycol ether ) solvent A liquid that can dissolve other substances (solutes) without any change in their chemical composition.

Application(s):	protic solvent A polar solvent that is capable of acting as a hydron (proton) donor. (via glycol ether ) solvent A liquid that can dissolve other substances (solutes) without any change in their chemical composition.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	2-methoxyethanol (CHEBI:46790) has role protic solvent (CHEBI:48356) 2-methoxyethanol (CHEBI:46790) has role solvent (CHEBI:46787) 2-methoxyethanol (CHEBI:46790) is a glycol ether (CHEBI:172390)

Incoming	2-methoxyethyl ester (CHEBI:136838) has functional parent 2-methoxyethanol (CHEBI:46790)

IUPAC Name

2-methoxyethanol

Synonyms	Sources
1-hydroxy-2-methoxyethane	ChemIDplus
2-hydroxyethyl methyl ether	NIST Chemistry WebBook
2-methoxy-1-ethanol	ChemIDplus
2-METHOXYETHANOL	PDBeChem
3-oxa-1-butanol	ChemIDplus
β-methoxyethanol	NIST Chemistry WebBook
HOCH₂CH₂OCH₃	NIST Chemistry WebBook
Methyl cellosolve	ChemIDplus
methyl oxitol	ChemIDplus
monomethyl ethylene glycol ether	ChemIDplus

Manual Xrefs	Databases
1639	PPDB
2-Methoxyethanol	Wikipedia
2-METHOXYETHANOL	MetaCyc
DB02806	DrugBank
MXE	PDBeChem
View more database links

Registry Numbers	Types	Sources
109-86-4	CAS Registry Number	ChemIDplus
109-86-4	CAS Registry Number	NIST Chemistry WebBook
1731074	Reaxys Registry Number	Reaxys
81877	Gmelin Registry Number	Gmelin

Citations

Pomierny B, Starek A, Krzyżanowska W, Starek-Swiechowicz B, Smaga I, Pomierny-Chamioło L, Regulska M, Budziszewska B (2013)
Potential neurotoxic effect of ethylene glycol ethers mixtures.
Pharmacological reports : PR 65, 1415-1421 [PubMed:24399739]
[show Abstract]

Nelson BK, Snyder DL, Shaw PB (2001)
Developmental toxicity interactions of methanol and radiofrequency radiation or 2-methoxyethanol in rats.
International journal of toxicology 20, 89-100 [PubMed:11354470]
[show Abstract]
This research was undertaken to determine potential interactions among chemical and physical agents. Radiofrequency (RF) radiation is used in numerous workplaces, and many workers are concurrently exposed to RF radiation and various chemicals. The developmental toxicity of RF radiation is associated with the degree and duration of hyperthermia induced by the exposure. Previous animal research indicates that hyperthermia induced by an elevation in ambient temperature can potentiate the toxicity and teratogenicity of some chemical agents. We previously demonstrated that combined exposure to RF radiation (10 MHz) and the industrial solvent, 2-methoxyethanol (2ME), enhanced teratogenicity in rats. Interactions were noted at even the lowest levels of 2ME tested, but only at hyperthermic levels of RF radiation. The purpose of the present research is to investigate if the interactive effects noted for RF radiation and 2ME are unique to these agents, or if similar interactions might be seen with other chemicals. Because methanol is widely used as a solvent as well as fuel additive, and, at high levels, is teratogenic in animals, we selected methanol as a chemical to address generalizability. Based on the literature and our pilot studies, 0, 2, or 3 g/kg methanol (twice, at 6-hour intervals) were administered on gestation day 9 or 13 to groups of 10 Sprague-Dawley rats. Dams treated on day 9 were given methanol and exposed to RF radiation sufficient to maintain colonic temperature at 41 degrees C for 60 minutes (or sham). Those treated on day 13 were given methanol plus either 0 or 100 mg/kg 2ME. Because we observed that methanol produced hypothermia, some groups were given the initial dose of methanol concurrently with the RF or 2ME, and others were given the first dose of methanol 1.5 hours prior to RF or 2ME. Dams were sacrificed on gestation day 20, and the fetuses were examined for external malformations. The results indicate that RF radiation or methanol on day 9 increased the incidence of resorbed fetuses, but no interactive effects were observed. The resorptions were highest in groups given the experimental treatments 1.5 hours apart. The higher dose of methanol also reduced fetal weights. Administration of 2ME or methanol on day 13 increased the rate of malformations, and there was evidence of a positive interaction between 2ME and methanol. Fetal weights were reduced by 2ME and methanol alone, but no interaction was observed. Also, separation of the dosing with the teratogens did not affect the results. These results point out that interactions in developmental toxicology, such as those of RF radiation, 2ME, and methanol that we have studied, are complex, and such interactions cannot be fully understood or predicted without more research. It is important that combined exposure effects be considered when developing both physical agent and chemical agent exposure guidelines and intervention strategies.

Last Modified

06 May 2021

ChEBI

CHEBI:46790 - 2-methoxyethanol

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